Process of converting carbohydrates into hydrocarbons.



UNITED STATES PATENT OFFICE.

ARTHUR HEINEMANN, OF LONDON, ENGLAND.

FROCESS 0F CONVERTING CARBQHYDRATES INTO HYDBOOABBONS.

N0 Drawing.

of compounds of carbon and hydrogen, particularly to compounds of theformula (/,,H or polymers thereof, enerally represented by the formula(C H The object of the invention is to obtain from carbohydrates ofcommon occurrence and cheap nature a compound of the for- This inventionrelates to the manufacture mula C H which can be readily converted lntohydrocarbons of 'a valuable nature, such, for instance, oils.

Since the carbohydrates of plants are unquestionably closely related tothe hydrocarbons formed in plants or through their agency it isreasonable to conclude that the former may be converted into the latter.

Hydrocarbons containing C H or multiples thereof under certaincircumstances are converted into derivatives of the carbohydrates. Forinstance the C H caoutchouc, when 'ozomzed is converted intoltevulinicacid C H O and its aldehyde C H O Geraniol and linalool, C HO, both olefinic terpene alcohols, give when oxidized besides othersubstances leevulinic acid.

That bodies containing the group C H O may be derived from sugars andother carbohydrates is well known. It istherefore quite logical to takeadvantage of this relationship in converting the common carbohydratesinto the more valuable hydrocarbons based on the same radical, viz.entadienyl,'C H For this purpose a carbohydrates and their derivativesmay be used, sugar, dextrin, starch, gums and cellulose being the mostsuitable.

be present invention consists in the man ufacture of a hydrocarbon ofthe form C H and its polymers (C,,H,,) from carbohydrates by firstconverting the carbohydrates into laevulinio acid and then reducing thelatter, as by treating it with certain compounds of sulfur and afterwardwith hydrogen.

Specification of Letters Patent. Application filed September 21, 1909.Serial No. 518,839.

England,

as camphor and essential hydrocarbon 'tenol may be directly thenreduced, either Patented Mar. 1, 1910.

In carrying out'the invention the carbohydrate, for example ordinarycane su ar or starch, is first converted by boiling wlth dilutehydrochloric or sulfuric acid into a compound containing the roupC,H,,namely laevulinic acid, C H O The laevuhnic acid oftheformulaCH-GOCH CH COOH. so obtained is then mixed with 1% parts of phosphorustrisulfid. This mixture is heated in a retort to 130140 C. At thistemperature a violent reaction takes place and an oily body of the thio.hene grou distils over, viz., thiotolene, C H The structural formula ofthis body is The conversion of the carbohydrate can also be effected bythe use ofphospho'rus pentasulfid, when oxythiotolene, viz. thiotenol,CH ,C H S'OH, will first be produced, the structural formula of which isThe thiotenol so obtained is then either reduced to thiotolene by meansof phosphorus, trisulfid or alternatively the thiotreated with hydrogenas hereinafter described.

In the case of the production ofthiotenol 3 parts of laevulinic acid ismixed with 2 partsof phosphorus pentasulfid and treated in the same wayas hereinbefore described.

Instead of using compounds of sulfur and phosphorus other compounds ofsulfur, for instance those with potassium, sodium, calcium, arsenic,etc. may be employed. Likewise sulfur alone, or such compounds assulfureted hydrogen, ammonium hydrosulfid, sulfur dioxid and the likemay be used.

The thiotolene (or thiotenol) obtained is by means of hydrogen alone orby reducting mixtures such as water-gas, in the following manner. Thethiotolene together with hydrogen'is passed through a tube or vesselheated to 500.700 C. and containing finely divided copper, nickel, iron,silver or the like. As a result is broken at the line marked ;',thesulfur liberated combining with the metalyfor instance in the case ofcopper, copper sulfid is formed. The excess of hydrogen present combineswith the free valencies of the carbon acts both on the copper sulfid,reducing it again to metallic copper and on the tlnotolene, the sulfurcontalned in thelat-ter being removed. The final product 1s C H amethylbutin, a hemiter ene, the structural formula of which is of t egeneral type C=C a H H A term erature of more than 700 (3., produces poymeric compounds.

eanova Instead of using ordinary hydrogen as above described nascenthydrogen prepared in any suitable manner may be used.

Havin described my invention what I claim an desire to secure by LettersPatent is The process of converting carboh drates into hydrocarbons ofthe formula H or multiples thereof which consists in first converting acarbohydrate into laevulinic acid, I

then producing a compound of the thiophene group rom the laevulinic acidby treating the same with .a bod containing he thio hene compound into ahydrocarbon of the a ovenamed composition by reduction with hydrogen ina heated tube or vessel containing finely divided metal; substantiallyas described herein.

In testimony whereof I have signed my name to this specification in thepresence of two subscribing witnesses.

ARTHUR HEINEMANN.

Witnesses:

ARTHUR F. ENNIS, F. L. RAND.

